Kissimmee Homes with Gated Community - Guard Community Features

Kissimmee Homes with Gated Community - Guard Community Features

Welcome to Kissimmee, Florida—a vibrant city that perfectly balances the excitement of theme parks with the charm of suburban living. Nestled just south of Orlando, Kissimmee is renowned for its warm climate, stunning natural beauty, and a plethora of recreational opportunities. With its close proximity to world-famous attractions like Walt Disney World, Universal Studios, and the beautiful Lake Tohopekaliga, Kissimmee is a dream destination for families, nature enthusiasts, and anyone seeking a lively lifestyle.

One of the standout features of Kissimmee is its inviting gated communities, offering an exclusive and secure living experience. These guard-gated neighborhoods provide peace of mind, allowing residents to enjoy their surroundings without worry. Imagine coming home to a beautifully landscaped community where security is a top priority, ensuring a safe haven for you and your loved ones.

Homes within these gated communities are designed with modern living in mind, featuring spacious layouts, upscale amenities, and often, stunning views of lush greenery or serene water bodies. Many of these neighborhoods boast resort-style amenities such as swimming pools, fitness centers, and clubhouses, perfect for social gatherings or simply unwinding after a long day.

Living in Kissimmee means embracing a lifestyle filled with adventure, community, and comfort. Whether you’re looking for a family home or a serene retreat, the gated communities in Kissimmee offer an unparalleled living experience that combines security, luxury, and the warmth of a tight-knit community. Discover your dream home in Kissimmee today, and step into a world of endless possibilities!

Newest Kissimmee Homes with Gated Community - Guard Community Features

$698,000
6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 7 SubDv. ⋅ 34747 Zip Code
Welcome to your ultimate vacation retreat, ideally located just 5 miles from Walt Disney World in the highly sought-after Windsor Hills Resort! This beautifully maintained 6-bedroom, 4-bathroom pool home offers the perfect combination of comfort, entertainment, and resort-style living, making it an excellent choice as a second home or high-performing short-term rental investment. The property has been meticulously cared for and features numerous significant upgrades, including luxury vinyl plank flooring throughout (2022), upstairs A/C (2020), downstairs A/C (2022), pool heater (2021), pool motor/pump (2023), pool safety fence (2023), and dishwasher (2026). The home also features a durable tile roof, offering added longevity and value. The main level includes a bedroom and full bathroom, ideal for guests or multi-generational living. Upstairs, you'll find two spacious suites plus three themed guest bedrooms, providing plenty of room for family and vacation guests. The garage has been converted into a fun-filled game room, creating additional entertainment space for all ages. Step outside to your private screened-in pool, the perfect place to relax and enjoy the Florida sunshine. The HOA fee includes lawn service, daily valet trash pickup, internet, and basic cable. Windsor Hills offers outstanding resort amenities, including 24/7 manned gated entry, a resort-style clubhouse and community pool, sports courts, putting green, and more. Conveniently located just minutes from Disney theme parks, major Central Florida attractions, dining, shopping, championship golf courses, airports, and Florida's famous beaches, this is an exceptional opportunity to own a turn-key vacation home in one of Central Florida's most desirable resort communities.

2536 Holtrock Street, Kissimmee
$549,000
3 Beds ⋅ 3 Baths ⋅ Four Seasons At Orlando Pb 3b & 4a SubDv. ⋅ 34747 Zip Code
Welcome to refined Florida living in the sought-after Four Seasons at Orlando 55+ community. Set on a **premium conservation-view homesite within walking distance of the clubhouse and amenities**, this beautifully upgraded Dominica model offers 2,360 square feet of thoughtfully designed living space and exceptional indoor-outdoor living. The home features **2 bedrooms, 2.5 bathrooms, and a dedicated office with a closet that can function as a third bedroom**. The private guest suite includes its own full bath, while the expanded primary suite offers **2 walk-in closets with custom built-ins** and an upgraded bath with dual vanities, granite countertops, and an oversized walk-in shower. The kitchen features **GE Profile appliances, enhanced lighting, additional outlets, and a redesigned pantry with custom shelving**. The laundry room includes added cabinetry and storage, while the office is enhanced with **wall-to-wall book shelves and a large custom desk**. Additional garage shelving and a separate storage area provide even more functionality. A true highlight is the private outdoor living space. **Seamless corner glass sliders** open to an expansive covered lanai overlooking the peaceful conservation setting. The custom summer kitchen includes a **gas grill, 2 burners, refrigerator, sink, and ample storage**, representing an estimated $17,000 investment. The beautifully landscaped yard features approximately **40 to 50 recently added plants**, professionally maintained pavers, and significant **drainage and erosion improvements already completed**. The home has been exceptionally well maintained and shows beautifully. **Furniture is negotiable, and TVs may remain.** Jimmy Buffett and Disney-themed memorabilia and media do not convey. Residents of **Four Seasons at Orlando** enjoy 24-hour guarded entry, a 13,000-square-foot clubhouse, 2 resort-style pools, spa, fitness center, tennis, pickleball, and bocce courts. HOA fees include exterior landscaping for truly low-maintenance living. Just minutes from **Walt Disney World®**, dining, shopping, and entertainment, this home combines a premium location, conservation views, meaningful upgrades, and resort-style living in one exceptional residence. **Schedule your private showing today and experience Four Seasons living for yourself.**

7789 Four Seasons Boulevard, Kissimmee
$655,000
8 Beds ⋅ 6 Baths ⋅ Windsor At Westside Ph 2b SubDv. ⋅ 34747 Zip Code
Imagine pulling into a community where every day feels like you're on vacation. Located in the 24/7 guard-gated community of Windsor at Westside, this sprawling 8-bedroom, 6-bathroom home spans over 4,000 square feet of space designed for bringing loved ones together. Best of all, it comes fully furnished and turnkey, making it completely move-in or rental-ready from day one. Whether you are looking for a short-term rental investment or a primary residence where family and friends can spread out, this property delivers comfort, luxury, and convenience. From the moment you walk through the front door, the open-concept layout feels welcoming and effortless. The main floor features durable tile flooring throughout the main living areas, centered around a kitchen with rich cabinetry, stone countertops, and a large island where everyone naturally gathers. Just off the main space, slide open the glass doors to your private, screened outdoor oasis, featuring a crystal-clear pool, relaxing spa, and covered brick-paver lanai perfect for outdoor dining and evening relaxation. Thoughtful main-floor planning sets this home apart. The main level includes a private primary bedroom suite, as well as a second full bedroom and guest bathroom—ideal for guests who prefer to avoid stairs or for multi-generational living arrangements. Upstairs and across all bedrooms, you will find newly updated low-maintenance LVP flooring. For added entertainment, the full garage game room comes ready for fun with billiards and air hockey. Beyond the home, the neighborhood offers a complete resort lifestyle. The community amenities include a zero-entry pool with a water slide, lazy river, clubhouse, fitness center, bar and lounge, convenience store, tennis courts, playground, private rentable cabanas and more. The HOA fee simplifies daily living by covering high-speed internet, cable TV, daily trash pick-up, and full lawn maintenance. The location places you close to Central Florida's top attractions. You are approximately 25 minutes from Walt Disney World, minutes from shopping and dining at Posner Park, and close to the dining, shopping, and entertainment options at the Promenade at Sunset Walk, as well as nearby championship golf at ChampionsGate and major roadways like I-4 and US-27. Opportunities like this don't wait long—reach out now to claim your piece of Central Florida resort living today!

1610 Lima Avenue, Kissimmee
$420,000
2 Beds ⋅ 2 Baths ⋅ Four Seasons At Orlando Ph 2 SubDv. ⋅ 34747 Zip Code
Welcome to the Four Seasons of Orlando's 55+ Community in Kissimmee, Florida just minutes from the Disney Theme Parks. This is a "Sandpiper" Villa with two bedrooms and two full baths plus a bonus room that can be an office or third bedroom. You will enjoy the spacious open concept living with sliders out to your own private heated pool. The caged lanai is extended with plenty of sunshine coming in. The Four Seasons is intertwined within Mystic Dunes Golf Course which makes for an interesting property lay-outs. We have a gate access over to the golf course and can enjoy lunch or dinner at the restaurant. You will also enjoy the two heated pools with a lap lane and hot tub. The clubhouse features a large ballroom, kitchen, game rooms, meeting rooms, gym and excercise room. Come join our community, it sure is a special place to live and minutes to the Disney Parks.

1896 Flora Pass Place, Kissimmee
$275,000
3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 2 SubDv. ⋅ 34747 Zip Code
Fully Furnished First Floor Condo Near Disney! This beautifully maintained 3 bedroom, 2 bathroom FIRST FLOOR condo in the gated Wyndham Palms Resort Community offers exactly that lifestyle, with the added benefit of being FULLY FURNISHED and APPROVED for SHORT TERM RENTALS and AIRBNB. Whether you are searching for a vacation home, an income producing investment, or a primary residence close to the parks, this property is ready to deliver from day one. The open concept layout centers around a kitchen with STAINLESS STEEL APPLIANCES (2025), flowing easily into the living and dining spaces. NEW LUXURY VINYL PLANK FLOORING, FRESH PAINT, and REPLACED WINDOWS throughout give the home a clean, updated feel, while BRAND NEW LIVING ROOM FURNITURE means it is truly move in ready. The split bedroom design offers privacy for owners and guests alike, and a dedicated office space adds flexibility for remote work or managing your rental. Both bathrooms feature new shower doors for a fresh, modern touch. Imagine mornings on your private patio with coffee in hand, evenings by the resort pool, and easy access to Walt Disney World whenever the mood strikes. Step outside and you are directly across from the clubhouse, where residents enjoy 24 hour guard gated security, a resort style pool, splash pad, jacuzzi, sand volleyball, tennis and basketball courts, a movie theater, game room, and more. Location is everything here. You are minutes from Walt Disney World, Margaritaville Resort Orlando, Island H2O Water Park, Sunset Walk, Celebration, Old Town, championship golf, and Orlando International Airport, with quick access to US 192, SR 429, I 4, and Osceola Parkway. This is more than a condo. It is a chance to own a piece of the Central Florida lifestyle, fully turnkey and ready for you to enjoy

2307 Butterfly Palm Way Unit 104, Kissimmee
$299,990
3 Beds ⋅ 3 Baths ⋅ Villas At Reunion Square Condo Ph 4 SubDv. ⋅ 34747 Zip Code
Beautiful furnished residence for sale at Meeting Resort We present an excellent opportunity to purchase a fully furnished house in one of the most valued communities of the meeting resort. This spacious unit has 3 bedrooms, 3 full bathrooms and a deposit right at the entrance, perfect for storing belongings with practicality. The large balcony offers a charming view, ideal for moments of relaxation and leisure. The open concept kitchen is modern and functional, equipped with all appliances, planned cabinets, quick meal counter and a complete laundry area ready for use. The condominium offers 24 -hour security, several internal amenities, exclusive Clubhouse, resort style pool and playground - all designed for the comfort and fun of the whole family. The location is privileged: close to everything you need, restaurants, markets and just a few minutes from Walt Disney World. Do not miss this unique opportunity to live or invest in a high standard property in the heart of Florida!

7651 Whisper Way Unit 201, Kissimmee
$474,000
4 Beds ⋅ 3 Baths ⋅ Solivita Ph 5-A SubDv. ⋅ 34759 Zip Code
Virtually Staged. Like-New Calabria Model with Water & Conservation Views and Private In-Law Suite! Welcome to this beautifully maintained 2019 Calabria model featuring 4 bedrooms, 3 bathrooms, a private in-law suite with separate entry, and stunning water and conservation views on a . Ideally located just minutes from the Village Amenities Center, this home offers the perfect combination of comfort, privacy, and convenience. Enter through the screened-in front walkway, where you’ll find the private entrance to the in-law suite as well as the impressive leaded-glass front door. Inside, you’ll discover a spacious open-concept living, dining, and kitchen area designed to take full advantage of the beautiful water and conservation views. The large kitchen features a generous eat-at island/bar, abundant cabinetry with convenient pull-out drawers, beautiful quartz countertops, and a walk-in pantry. The adjoining dining area provides a wonderful view of the screened lanai, water, and conservation area. The spacious primary bedroom offers a tray ceiling, ceiling fan, and a peaceful private view of the water and conservation area. The luxurious primary bath features dual sinks, a large custom walk-in shower, and an enormous walk-in closet with enough room to feel like a small bedroom. Two additional guest bedrooms are located on the opposite side of the home, providing privacy for family or guests. These rooms can also easily be used as den, office, or flex spaces, with a conveniently located bathroom between them. The private in-law suite is accessed through its own separate entrance from the screened front walkway and includes a full bathroom, making it ideal for extended family, overnight guests, or a private retreat. Step outside to the screened and covered lanai, where you can relax and enjoy peaceful water and conservation views. It’s the perfect spot for morning coffee, entertaining, or simply enjoying the Florida lifestyle. The spacious two-car garage provides plenty of storage, along with a golf cart hookup and attic storage space. Additional benefits include windows, doors, and construction features designed to meet current hurricane-code standards, which will qualify the home for available new-home and hurricane-protection insurance discounts. The property is also NOT in a flood zone (Zone X). This exceptional Calabria model combines a desirable floor plan, private in-law suite, beautiful views, abundant storage, and a fantastic location near the Village Amenities Center. A must-see home that truly feels like new! The HOA provides exceptional value by covering landscaping maintenance, irrigation, cable TV, and high-speed Internet, allowing you to enjoy a low-maintenance lifestyle in this desirable community. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy a fully 2 equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

163 Olympus Way, Kissimmee
$459,990
4 Beds ⋅ 3 Baths ⋅ Cove At Storey Lake 4 SubDv. ⋅ 34746 Zip Code
Welcome to this beautifully furnished 4-bedroom, 3-bathroom townhome located in the highly desirable Storey Lake Resort! This turnkey vacation home offers the perfect combination of personal enjoyment and short-term rental potential, just minutes from Walt Disney World and Central Florida’s world-famous attractions. The open-concept floor plan features a modern kitchen with stainless steel appliances, spacious living and dining areas, and sliding doors leading to your private screened-in pool—perfect for relaxing after a day at the parks. One bedroom and full bathroom are conveniently located on the first floor, with the primary suite and additional bedrooms upstairs. Storey Lake Resort offers exceptional amenities including resort-style pools, a lazy river, water slides, fitness center, mini golf, playgrounds, basketball courts, clubhouse, and more. Conveniently located near Disney, shopping, dining, and major highways. Fully furnished and ready for your next vacation or investment opportunity!

4192 Paragraph Drive, Kissimmee
$560,000
6 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
THE SELLER IS VERY MOTIVATED TO SELL!!!! Exceptional Vacation Home in Solara Resort – Private Pool, Short-Term Rental Approved & Minutes from Walt Disney World®! Welcome to this stunning fully furnished vacation home located in the highly sought-after Solara Resort, one of Central Florida's premier resort communities for short-term rentals. Whether you're looking for a profitable investment property, a vacation retreat, or a second home, this property offers the perfect combination of luxury, comfort, and location. From the moment you arrive, you'll be welcomed by a charming covered front porch and an inviting entryway leading into a bright, open-concept living area. Large sliding glass doors fill the home with natural light and open to a covered lanai overlooking the private screened-in pool, creating the perfect indoor-outdoor living space for relaxing or entertaining. The spacious kitchen is designed for both functionality and style, featuring solid wood cabinetry, a large breakfast bar, generous counter space, and a full set of appliances, making meal preparation effortless. This beautiful home offers 6 spacious bedrooms, 4 full bathrooms, and 1 half bath, plus a versatile upstairs loft ideal as a second family room or game area. The primary suite is conveniently located on the first floor and features a large walk-in closet and an elegant en-suite bathroom with dual vanities and plenty of space. Several bedrooms are professionally decorated with themed designs, creating an unforgettable experience for guests of all ages. The home also includes a 1-car garage. As part of the renowned Solara Resort, owners and guests enjoy access to world-class resort amenities, including a spectacular resort-style pool, FlowRider® surf simulator, clubhouse, fitness center, restaurant and poolside bar, splash pad, water slides, sports simulator, basketball court, beach volleyball court, soccer field, playground, game room, walking areas, and a gated entrance with resort-style security. Ideally located just minutes from Walt Disney World® Resort, Disney's Animal Kingdom, shopping, restaurants, golf courses, major highways, Island H2O Water Park, Sunset Walk, and other world-famous Orlando attractions, this home offers exceptional convenience for both owners and vacation guests. Don't miss this incredible opportunity to own a high-demand vacation home in one of Kissimmee's most desirable resort communities. Schedule your private showing today!

9012 Egret Mills Terrace, Kissimmee
$648,000
7 Beds ⋅ 7 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Step into your next high-performing investment at 1633 Nassau Point Trail! This breathtaking, fully furnished 7-bedroom, 6.5-bathroom retreat in the premier gated Solara Resort is a proven revenue generator built for ultimate guest satisfaction. Perfectly positioned just steps from the clubhouse and adjacent to convenient extra guest parking, this turnkey powerhouse delivers high-yield performance alongside effortless vacation living. Guests can cool off in the private screened-in pool and spa, catch the big game on multiple outdoor TV setups, or unwind in the air-conditioned, tiki-themed garage lounge—a massive hit for both adults and teens. Inside, custom hand-painted murals and immersive themed bedrooms elevate the guest experience, driving stellar reviews and consistent bookings. The numbers speak for themselves: this top-performing property boasts an impressive 70% overall occupancy rate over the last 12 months, surging to an incredible 82% occupancy so far in 2026. For savvy investors or vacation home buyers, Solara Resort offers unmatched marketing power, attracting global travelers directly and through travel agency networks, as well as major booking platforms. The resort itself is a major draw, featuring world-class amenities, including the famous FlowRider® surf simulator, a zero-entry pool, a splash pad, a fitness center, a bar and grill, and sports courts. Located just minutes from Orlando’s world-renowned theme parks, premier dining, and top shopping destinations, this income-generating asset is completely plug-and-play and ready to start delivering returns from day one.

1633 Nassau Point Trail, Kissimmee
$270,000
2 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Fully furnished 2-bedroom, 2.5-bath townhome in Regal Oaks Resort, conveniently located next to Old Town and minutes from Central Florida’s top attractions, shopping, dining, and entertainment. The home features a private rear setting with mature trees providing a natural privacy buffer from neighboring properties. The main level includes an open living and dining area, a well-appointed kitchen with stainless steel appliances and granite countertops, and convenient access to the outdoor living space. Upstairs, both bedrooms feature private en-suite bathrooms, making the layout ideal for both owners and guests. Regal Oaks offers resort-style amenities, including a pool complex, renovated ZAC’s Sports Bar & Grill, clubhouse, and more. Whether you’re looking for a vacation property, investment opportunity, or your own Central Florida getaway, this furnished townhome offers a convenient location within one of the area’s established resort communities.

2711 Coupe Street, Kissimmee
$338,000
4 Beds ⋅ 3 Baths ⋅ Bellavida Ph 1 SubDv. ⋅ 34746 Zip Code
Welcome to Bella Vida Resort! This beautifully maintained home offers a fantastic opportunity to own a property in one of Kissimmee’s popular resort-style communities. Featuring a spacious and comfortable layout, this home is ideally located near world-class theme parks, dining, shopping, and major highways. Bella Vida residents enjoy an array of resort-style amenities, including a clubhouse, community pool, fitness center, and recreational areas. Whether you are looking for a vacation home, investment property, or primary residence, this home offers an excellent combination of location, comfort, and convenience. Don’t miss the opportunity to make this Bella Vida property your own!

1050 Las Fuentes Drive, Kissimmee
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